Kristin has just had to close her small Manhattan clothing boutique to return to her Ohio home town and live in her parents' former home. It's an adjustment for Kristin and her young daughter— especially when she runs into her former high school rival. Kristen and Emily struggle to find their new normal with the help of the hunky local music teacher.

Adventurous flight attendant Sydney’s plans for a tropical Christmas get delayed when she helps an unaccompanied minor get home to Chicago to her dad Jonathan, a handsome widower and investigative reporter. Faced with a shortage of out-going flights, Sydney is marooned for several days in the Windy City – once her home as a small girl — and tags along with Jonathan, his daughter, and their exuberantly festive family until she can find a connecting flight. Jonathan makes her a deal: he helps her chase down the story of how her late parents met, and she helps him to write the perfect Christmas story and keep his job, and along the way, sparks form between them.